Dare to explore
A year in review from my Lisbon office

Dare to explore

Reflection on the last year


This morning I came back to the office following the festive season. With a pretty foggy mind, unclear how to get going and what to prioritise as I move into my second year of being an entrepreneur and founder of Squadra .

Maybe that's because the time away from my computer those past few weeks was really good, enjoying the slower pace of life and spending quality time with my wife and our kids. Making it harder to re-ignite the internal engine and self drive.

Whatever the root cause of that emotion, I thought that the best use of my time would be to look into all that I and the collective at Squadra have been able to accomplish, as well as sharing a few lessons learnt along the way of transitioning away from full time executive to my first ever "true" entrepreneur endeavour.

Hopefully, there are a few things you find resonance with as you reflect on your own executive journey and what lies ahead for you as a new chapter opens.


2023 highs

  • Trained as an executive coach by the Co-Active Training Institute
  • Got selected to join Co Lab , a collective of coaches supporting series A upwards startups in the US and Australia. Founded by serial entrepreneur and investor Maxine Minter
  • Coached 16 individuals, mainly CEO's and C levels accumulating in excess of 200 hours in less than one year
  • Launched Squadra , a collective of now 35 senior leaders offering on demand mentoring, fractional C levels and leadership coaching. Bootstrapped and profitable.
  • Generated a revenue corresponding to 50% of what I made as an executive ( see below as this is also a low )
  • Worked harder than ever, but more aligned with my life purpose and values. Leading to greater fulfilment and balance
  • I journaled every Sunday evening. That's probably the first ever routine I stick to aside of breakfast...


2023 Lows

  • I can be quite restless. Doing too many things. Along the year, I became more disciplined and got much better at saying no. Still, this is a saboteur behaviour to keep in check. Do you want to map out your own saboteurs ? I recommend this free tool from Positive Intelligence
  • Quite naively I thought my coaching practice would take off faster and that I would be able to charge higher rates sooner. On the bright side, I could bridge that revenue gap by taking on a fractional mandate as the Strategy Officer for leading hospitality brand Vida Plena currently leading a fascinating regenerative farming project on a 28Ha land in Portugal.
  • Over the first half of the year, I neglected my fitness and mental health giving pretty much all my bandwidth to my work and family. Leading to fatigue, excess of weight and the worsening of a chronic lower back pain. I now have a better set up with Yoga 2 to 3 times a week Down Dog and more importantly a much greater understanding of the mind body connection thanks to Curable . Which not only help me reduce the frequency and severity of back pain, but improves my mood and energy levels.


A few takeaways for you ?

  • It's never too late to reshuffle your cards or explore new paths. I started to train as an executive coach at 48 years old and launched Squadra just a few days prior to turning 49. As we grow older, we become more risk adverse. That's possibly the best recipe to obsolescence in a rapidly changing world. Keep daring. You're more resourceful than you think.
  • My transition from full time exec to full time coach was an illusion in terms of velocity. If you are to consider a career shift, look at ways you can mitigate the risks. In that regards, taking on a fractional mandate can help you generate a solid revenue base while investing some of your time and money towards your new endeavour.
  • It's indeed very lonely at the top especially when being a solopreneur. But it does not have to be that way. Join a collective, build your support network, take a coach
  • Look after your mental and fitness health. Any change is difficult and while it will look counter intuitive to slow down and dedicate time for yourself when you passionately build something new, this is the foundation to optimal and sustainable performance


I look at this past year with a great sense of pride, having grown personally in the most significant manner if I look at the last decade. Taking that leap would not have been possible with the nudge, inspiration and cheering of some very special people.

With the risk of forgetting a few beautiful beings, I want to express my gratitude to the following people Carolina Annand ( my wife and greatest supporter ), Stephanie Usry Ellen Donnelly ( for coaching me and creating that spark ), Maxine Minter Sasza Lohrey and the entire team Co Lab for their trust, Matt Ellis for his genius and generous work on brand strategy and design on Squadra and to all the members of the Squadra collective Alejandro Litovsky Earth Security Andreas Creten madewithlove Bill Cogan Seven Legal Lisa D'Amico Julien De Visscher Human37 Dhruv Menon Julien Dulioust Elsa Hermal Eugenia Carrara Frederic Chanay Jean-Charles Gaudechon Marjolaine Grondin Albert Hill The Modern House Irene Liu Hypergrowth GC Jacopo Tonoli PEAK Sport Media Joe Tan Louise Heite David Navarro Marilyn Edmunds Bowser Marsha Meredith Madderlake Designs Matthias Schaefer Pauline Pham Renzo Procaccini Roann Ghosh Robert Bainbridge FCIPD Sorcha Lorimer Stephanie Usry Thomas Van Halewyck Arthur de Catheu



Thanks for your candor and nudge for all to be bold and explore in the new year ahead!

Ellen Donnelly

Business coach for entrepreneurs and creator of Monday Mornings, a newsletter exploring the ‘shift to mass entrepreneurialism’ future of work.

1 年

Loved working with you, Benoit and seeing your incredible journey evolve!

Pour mieux avancer, il est nécessaire de retourner en arrière pour mieux faire face à l'avenir. Merci pour le partage Beno?t.

Beno?t Simeray

Founder of Squadra.team, a collective of 50+ fractional leaders | Executive Coach | 17+ Years C-Level Experience scaling VC-Backed Ventures from Pre-Revenue to $1BN+ across ???? and ????

1 年

cc Jean de La Rochebrochard if you want to follow my candid reflection on 2023 and more relevant the emergence of the #sharedleadership economy.

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